73451-86-2Relevant academic research and scientific papers
Total synthesis of aphadilactones A-D
Yin, Jian-Peng,Gu, Min,Li, Ying,Nan, Fa-Jun
, p. 6294 - 6301 (2014/07/21)
The first total synthesis of aphadilactones A-D, diastereomeric natural products recently isolated from the Meliaceae plant Aphanamixis grandifolia by Yue and co-workers, which possess an unprecedented carbon skeleton, has been achieved. The synthesis features a catalytic asymmetric hetero-Diels-Alder reaction to form the dihydropyran ring, concurrent installation of the lactone and furan moieties via a tandem acid-catalyzed acetal cleavage, oxidation, and cyclization process, and an intermolecular Diels-Alder reaction to forge the target products.
Unsaturated Acyl Derivatives of Silicon, Germanium, and Tin from Metalated Enol Ethers
Soderquist, John A.,Hassner, Alfred
, p. 1577 - 1583 (2007/10/02)
The preparation of 1-lithio derivatives of some conjugated vinyl ethers is described.Reaction of these compounds with the chlorotrimethyl derivatives of silicon, germanium, and tin gives the corresponding metallovinyl ethers in 50-80percent yield.At least in the case of silicon these reactions proceed with retention of stereochemistry.The silyl compounds undergo Z E photoisomerization.Hydrolysis of the ethers in aqueous acetone gives the corresponding acylmetallanes in 60-75percent yield.The metalation and hydrolysis reactions are examined in some detail.The spectral properties of these novel unsaturated acylmetallanes are presented and discussed.
